Production and use of dimers of hematoporophyrin, purpurins, chlorines and purpurin- and chlorin-complexes

Claim 1

A dimer of (1) a purpurin or a purpurin metal complex having the structure of any of FIGS. 1, 7, 14-18, 29-38, 44-48 or 54-58 of the attached drawings, or a chlorin or a chlorin metal complex having the structure of any of FIGS. 2, 8, 19-28, 39-43 or 49-53 of the attached drawings and (2) hematoporphyrin or a purpurin or a purpurin metal complex having the structure of any of FIGS. 1, 7, 14-18, 29-38, 44-48 or 54-58 of the attached drawings, or a chlorin or a chlorin metal complex having the structure of any of FIGS. 2, 8, 19-28, 39-43 or 49-53 of the attached drawings, wherein each of R10 through R13 and R16 is hydrogen, and each of R1 through R9, R14 and R15 is: H or CHO, an alkyl group having from 1 to 4 carbon atoms, excluding tertiary butyl, an alkylene group having from 2 to 4 carbon atoms, a group having the formula R 2 N(R 3 ) 2 where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; R 3 is hydrogen or an alkyl group having from 1 to 2 carbon atoms and the two R 3 groups can be the same or different, a group having the formula R 2 N(R 4 ) 3 A where R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond; A is a physiologically acceptable anion; and R 4 is an alkyl group having from 1 to 2 carbon atoms and the three R 4 groups can be the same or different, a group having the formula R 2 OH were R 2 is a bivalent aliphatic hydrocarbon radical having from 1 to 4 carbon atoms, wherein any carbon to carbon bond is either a single or a double bond, and not more than one is a double bond, CO 2 R', CH 2 CO 2 R' or CH 2 CH 2 CO 2 R', where R' is hydrogen or an alkyl group having from 1 to 4 carbon atoms, excluding tertiary butyl, an amino acid moiety which is attached to the purpurin or chlorin moiety through a carbonyl which is a part of an amide produced by reaction between an amine function of a naturally occurring amino acid and a CO 2 R', CH 2 CO 2 R' or CH 2 CH 2 CO 2 R' group of the purpurin or chlorin, a monoclonal antibody moiety which selectively binds to malignant tumors and is attached to the purpurin or chlorin moiety through a carbonyl which is a part of an amide produced by reaction between an amine funtion of a monoclonal antibody and a CO 2 R', CH 2 CO 2 R' or CH 2 CH 2 CO 2 R' group of the purpurin or chlorin, or in the purpurins and purpurin metal complexes of FIGS. 1, 7 14-18, 34-38 and 54-58 and in the chlorins and chlorin metal complexes of FIGS. 2 and 8 R1 can be a bivalent aliphatic hydrocarbon radical having from 2 to 4 carbon atoms wherein both of the valences of the radical are attached to the same carbon atom thereof and to a carbon atom of the purpurin, chlorin, or metal complex, and in the purpurins and purpurin metal complexes of FIGS. 29-33 and of FIGS. 44-48 and in the chlorins and chlorin metal complexes of FIGS. 19-28, 39-43 and 49-53, both R1 and R2 can be bivalent aliphatic hydrocarbon radicals having from 2 to 4 carbon atoms wherein both of the valences of the radical are attached to the same carbon atom thereof and to a carbon atom of the purpurin or metal complex, and M comprises a metal cation that is complexed with two of the nitrogens of the purpurin or chlorin and is Ag, Al, Ce, Co, Cr, Dy, Er, Eu, Fe, Ga, Gd, Hf, Ho, In, La, Lu, Mn, MO, Nd, Pb, Pd, Pr, Pt, Rh, Sb, Sc, Sm, Sn, Tb, Th, Ti, Tl, Tm, U, V, Y, Yb, Zn or Zr, said dimer being the product of reaction between a CO 2 R', CH 2 CO 2 R' or CH 2 CH 2 CO 2 R' group of the (1) purpurin, chlorin or metal complex or of the (2) hematoporphyrin, purpurin, chlorin or metal complex and an amino nitrogen or an alcoholic OH group of the other, with the proviso that not more than one of R1 through R9, R14 and R15 is CHO, a group having the formula R 2 N(R 3 ) 2 , a group having the formula R 2 N(R 4 ) 3 A, an amino acid moiety or a monoclonal antibody moiety.